Synthesis and Crystal Structures of Two New Schiff Base Hydrazones Derived from Biphenyl-4-Carbohydrazide |
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Authors: | Grzegorz Dutkiewicz B Narayana S Samshuddin H S Yathirajan Maciej Kubicki |
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Institution: | (1) Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznan, Poland;(2) Department of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India;(3) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570 006, India; |
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Abstract: | Abstract The crystal structures of two novel Schiff base hydrazones have been determined by means of the X-ray diffraction. These compounds:
N′-(E)-(2,5-dimethoxyphenyl)methylidene]biphenyl-4-carbohydrazide, C22H20N2O3 (1) and N′-(E)-(4-fluorophenyl)methylidene]biphenyl-4-carbohydrazide, C20H15FN2O (2), are the first structurally characterized biphenyl derivatives of phenylmethylidene-carbohydrazide. Both compounds crystallize
in the monoclinic space groups, 1 in P21/c space group with a = 13.987(2) ?, b = 16.426(3) ?, c = 8.214(2) ?, β = 98.12(2)°, and 2 in C2/c with a = 37.163(5) ?, b = 10.696(2) ?, c = 8.098(2) ?, β = 101.18(2)°. Both molecules have very similar bond lengths and angles pattern, even in the differently substituted
phenyl ring. However, the conformations of the molecules differ significantly, the more crowded molecule 1 is much more folded than 2. The dihedral angle between the terminal ring planes is 56.17(6)° in 1 while in 2 it is as small as 2.83(14)°. In both structures relatively short and linear N–H···O hydrogen bonds (created by the best available
hydrogen bond donor and acceptor) connect molecules into the chains along the unit cell parameter of ca. 8 ? in length. The
next stage of the crystal architecture determination, the secondary interactions, are however quite different: in 1 there are almost solely dispersion van der Waals interactions while in 2 some more specific C–H···F and C–H···π interactions are also involved in the crystal packing. |
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